Substituted imide derivatives

ABSTRACT

The present invention relates to novel substituted imide derivatives of the general formula (I)                    
     in which 
     R 1  represents optionally substituted cycloalkyl, 
     R 2  represents optionally substituted alkyl or optionally substituted cycloalkyl, 
     R 3  represents alkyl, alkoxy, alkylthio, amino, alkylamino or dialkylamino and 
     R 4  represents cyano or nitro, 
     and to processes for their preparation and to their use for controlling animal pests and as herbicides.

The present application relates to novel substituted imide derivatives,to a process for their preparation and to their use for controllinganimal pests and as herbicides.

Certain imide derivatives are already known (cf. WO 91/04 965, WO 93/04032, EP-A-403 159; J. Organomet. Chem. (1975), 97 (1), pp. 39-44; Bul.Soc. Chim. Belg. (1981), 90 (1), pp. 89-98). Insecticidal and/orherbicidal properties of some of these compounds have also beendisclosed.

This invention, accordingly, provides novel substituted imidederivatives of the general formula (I)

in which

R¹ represents optionally substituted cycloalkyl,

R² represents optionally substituted alkyl or optionally substitutedcycloalkyl,

R³ represents alkyl, alkoxy, alkylthio, amino, alkylamino ordialkylamino and

R⁴ represents cyano or nitro.

If appropriate, the imide derivatives of the formula (I) can also bepresent as optical and/or geometrical isomers. The present inventionrelates both to the various isomer mixtures and to the pure isomers.

The novel substituted imide derivatives of the formula (I) are obtainedwhen amines of the formula (II)

in which

R¹ and R² are as defined above are reacted with ethaneimidate of theformula (III)

 in which

R³ and R⁴ are as defined above,

R⁵ represents alkyl and X represents oxygen or sulphur in the presenceof a diluent.

The novel imideamide derivatives of the general formula (I) have highlypronounced biological properties and are particularly suitable forcontrolling animal pests, such as insects, arachnids and in particularnematodes, encountered in agriculture, in forests, in the protection ofstored products and materials and in the hygiene sector; for controllinganimal pests, such as parasitic nematodes, in veterinary medicine; andalso for use as herbicides.

The formula (I) provides a general definition of the compounds accordingto the invention. Preferred substituents or ranges of the radicalslisted in the formulae above and below are illustrated below.

R¹ preferably represents C₃-C₆-cycloalkyl which is optionally mono- totrisubstituted by identical or different substituents from the groupconsisting of halogen, C₁-C₄-alkyl, C₁-C₄-alkoxy and C₁-C₄-alkylthio.

R² preferably represents C₁-C₄-alkyl which is optionally substituted byhalogen, cyano or C₁-C₄-alkoxy or represents C₃-C₆-cycloalkyl which isoptionally mono- to trisubstituted by identical or differentsubstituents from the group consisting of halogen, C₁-C₄-alkyl,C₁-C₄-alkoxy and C₁-C₄-alkylthio.

R³ preferably represents C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-alkylthio,amino, C₁-C₄-alkylamino or di-(C₁-C₄)-alkylamino.

R¹ particularly preferably represents cyclopentyl or cyclohexyl, each ofwhich is optionally mono- to trisubstituted by identical or differentsubstituents from the group consisting of fluorine, chlorine, bromine,methyl, ethyl, methoxy, ethoxy, methylthio and ethylthio.

R² particularly preferably represents methyl, ethyl or n- or i-propyl,each of which is optionally substituted by cyano, fluorine, chlorine,methoxy or ethoxy; or represents cyclopentyl or cyclohexyl, each ofwhich is optionally mono- to trisubstituted by identical or differentsubstituents from the group consisting of fluorine, chlorine, bromine,methyl, ethyl, methoxy, ethoxy, methylthio and ethylthio.

R³ particularly preferably represents methyl, ethyl, n- or i-propyl; n-,i-, s- or t-butyl; methoxy, ethoxy, n- or i-propoxy; methylthio,ethylthio, n- or i-propylthio; amino; methylamino, ethylamino, n- ori-propylamino; ethylmethyl-amino, dimethylamino, diethyl amino,methyl-n-propyl -amino, methyl-i-propylamino, ethyl-n-propyl-amino,ethyl-i-propyl-amino, i-propyl-n-propyl-amino or diisopropylamino.

R¹ very particularly preferably represents cyclopentyl or cyclohexyl,each of which is optionally mono- or disubstituted by identical ordifferent substituents from the group consisting of chlorine, methyl andmethoxy.

R² very particularly preferably represents methyl, ethyl or isopropyl.

R³ very particularly preferably represents methyl, ethyl, isopropyl;methoxy, ethoxy, isopropoxy; methylthio, ethylthio, isopropylthio;amino; methylamino, ethylamino; dimethylamino, ethylmethylamino ordiethylamino.

In the definitions, the hydrocarbon chains, such as, for example, alkyl,are in each case straight-chain or branched.

Preference according to the invention is given to those compounds of theformula (I) which contain a combination of the meanings listed above asbeing preferred.

Particular preference according to the invention is given to thosecompounds of the formula (I) which contain a combination of the meaningslisted above as being particularly preferred.

Very particular preference according to the invention is given to thosecompounds of the formula (I) which contain a combination of the meaningslisted above as being very particularly preferred.

Using, for example, R-(−)-cyclohexylamine and methylthioN-cyano-ethaneimidate as starting materials, the course of the reactionof the process according to the invention can be represented by thefollowing equation:

The amines of the formula (II) required as starting materials forcarrying out the process according to the invention are generally knowncompounds of organic chemistry and/or obtainable in a generally knownmanner. The cyclohexylamine derivatives of the formula (II) can beobtained particularly advantageously by hydrogenation of thecorresponding phenylamine derivatives.

The formula (III) provides a general definition of the ethaneimidatesfurther to be used as starting materials in the process according to theinvention. In this formula, R⁵ preferably represents C₁-C₄-alkyl, suchas, in particular, methyl or ethyl.

Most of the N-cyano-ethaneimidates are known (cf., for example, J. Org.Chem. 28, 1816 (1963); Chem. Berichte 100, 2604 (1967); TetrahedronLetters 1968, 5523; Synthesis 1975, 332; J. Org. Chem. 35, 2067 (1970);U.S. Pat. No. 3,910,928) and/or they can be obtained by customaryprocesses.

Some of the N-nitro-ethaneimidates are also known (cf., for example, J.Org. Chem. USSR (English) 9 (1973), 1233-1236; JACS 76 (1954), 1877;Rec. Trav. Chim. Pay-Bas 81, 69 (1962); JP-A-0156947), and/or they canbe obtained by customary processes, such as, in particular, by customarynitration of the corresponding NO₂-free ethaneimidates of the formula(III).

The process according to the invention is preferably carried out in thepresence of a diluent. Preference is given to using alcohols, such asmethanol and ethanol; nitrites, such as acetonitrile, or esters, such asethyl acetate. It is also possible to carry out the process in water ororganic/aqueous mixtures.

When carrying out the process according to the invention, preference isgiven to using equimolar amounts; however, it is also possible to employan excess of one or the other starting material.

When carrying out the process according to the invention, the reactiontemperatures can be varied within a relatively wide range. In general,the process is carried out at temperatures between 0° C. and 100° C.,preferably between 20° C. and 80° C.

Work-up and isolation of the end products are carried out in a generallyknown manner.

The active compounds are suitable for controlling animal pests, inparticular insects, arachnids and nematodes, which are encountered inagriculture, in forests, in the protection of stored products and ofmaterials, and in the hygiene sector, and have good plant tolerance andfavourable toxicity to warm-blooded animals. The active compounds areparticularly suitable for controlling nematodes. They may be preferablyemployed as crop protection agents. They are active against normallysensitive and resistant species and against all or some stages ofdevelopment. The abovementioned pests include:

From the order of the Isopoda, for example, Oniscus asellus,Armadillidium vulgare and Porcellho scaber.

From the order of the Diplopoda, for example, Blaniulus guttulatus.

From the order of the Chilopoda, for example, Geophilus carpophagus andScutigera spp.

From the order of the Symphyla, for example, Scutigerella immaculata.

From the order of the Thysanura, for example, Lepisma saccharina.

From the order of the Collembola, for example, Onychiurus armatus.

From the order of the Orthoptera, for example, Acheta domesticus,Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus spp. andSchistocerca gregaria.

From the order of the Blattaria, for example, Blatta orientalis,Periplaneta americana, Leucophaea maderae, Blattella germanica.

From the order of the Dermaptera, for example, Forficula auricularia.

From the order of the Isoptera, for example, Reticulitermes spp.

From the order of the Phthiraptera, for example, Pediculus humanuscorporis, Haematopinus spp., Linognathus spp., Trichodectes spp. andDamalinia spp.

From the order of the Thysanoptera, for example, Hercinothripsfemoralis, Thrips tabaci, Thrips palmi and Frankliniella accidentalis.

From the order of the Heteroptera, for example, Eurygaster spp.,Dysdercus intermedius, Piesma quadrata, Cimex lectulanrus, Rhodniusprolixus and Triatoma spp.

From the order of the Homoptera, for example, Aleurodes brassicae,Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicorynebrassicae, Cryptomyzus ribis, Aphis fabae, Aphis pomi, Eriosomalanigerum, Hyalopterus arundinis, Phylloxera vastatrix, Pemphigus spp.,Macrosiphum avenae, Myzus spp., Phorodon humuli, Rhopalosiphum padi,Empoasca spp., Euscelis bilobatus, Nephotettix cincticeps, Lecaniumcorni, Saissetia oleae, Laodelphax striatellus, Nilaparvata lugens,Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spp. and Psyllaspp.

From the order of the Lepidoptera, for example, Pectinophoragossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletisblancardella, Hyponomeuta padella, Plutella xylostella, Malacosomaneustria, Euproctis chrysorrhoea, Lymantria spp., Bucculatrixthurberiella, Phyllocnistis citrella, Agrotis spp., Euxoa spp., Feltiaspp., Earias insulana, Heliothis spp., Mamestra brassicae, Panolisflammea, Spodoptera spp., Trichoplusia ni, Carpocapsa pomonella, Pierisspp., Chilo spp., Pyrausta nubilalis, Ephestia kuehniella, Galleriamellonella, Tineola bisselliella, Tinea pellionella, Hofmannophilapseudospretella, Cacoecia podana, Capua reticulana, Choristoneurafumiferana, Clysia ambiguella, Homona magnanima, Tortrix viridana,Cnaphalocerus spp. and Oulema oryzae.

From the order of the Coleoptera, for example, Anobium punctatum,Rhizopertha dominica, Bruchidius obtectus, Acanthoscelides obtectus,Hylotrupes bajulus, Agelastica alni, Leptinotarsa decemlineata, Phaedoncochleariae, Diabrotica spp., Psylliodes chrysocephala, Epilachnavarivestis, Atomaria spp., Oryzaephilus surinamensis, Anthonomus spp.,Sitophilus spp., Otiorrhynchus sulcatus, Cosmopolites sordidus,Ceuthorrhynchus assimilis, Hypera postica, Dermestes spp., Trogodermaspp., Anthrenus spp., Attagenus spp., Lyctus spp., Meligethes aeneus,Ptinus spp., Niptus hololeucus, Gibbium psylloides, Tribolium spp.,Tenebrio molitor, Agriotes spp., Conoderus spp., Melolontha melolontha,Amphimallon solstitialis, Costelytra zealandica and Lissorhoptrusoryzophilus.

From the order of the Hymenoptera, for example, Diprion spp., Hoplocampaspp., Lasius spp., Monomorium pharaonis and Vespa spp.

From the order of the Diptera, for example, Aedes spp., Anopheles spp.,Culex spp., Drosophila melanogaster, Musca spp., Fannia spp., Calliphoraerythrocephala, Lucilia spp., Chrysomyia spp., Cuterebra spp.,Gastrophilus spp., Hyppobosca spp., Stomoxys spp., Oestrus spp.,Hypoderma spp., Tabanus spp., Tannia spp., Bibio hortulanus, Oscinellafrit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae,Tipula paludosa, Hylemyia spp. and Liriomyza spp.

From the order of the Siphonaptera, for example, Xenopsylla cheopis andCeratophyllus spp.

From the class of the Arachnida, for example, Scorpio maurus,Latrodectus mactans, Acarus siro, Argas spp., Ornithodoros spp.,Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora,Boophilus spp., Rhipicephalus spp., Amblyomma spp., Hyalomrma spp.,Ixodes spp., Psoroptes spp., Chorioptes spp., Sarcoptes spp., Tarsonemusspp., Bryobia praetiosa, Panonychus spp., Tetranychus spp.,Hemitarsonemus spp., and Brevipalpus spp.

The phytoparasitic nematodes include, for example, Pratylenchus spp.,Radopholus similis, Ditylenchus dipsaci, Tylenchulus semipenetrans,Heterodera spp., Globodera spp., Meloidogyne spp., Aphelenchoides spp.,Longidorus spp., Xiphinema spp., Trichodorus spp. and Bursaphelenchusspp.

In particular, the compounds of the formula (I) according to theinvention have good nematicidal activity. Thus, they can be used withparticularly good results, for example, for controlling Meloidogyneincognita.

The active compounds according to the invention can be used asdefoliants, desiccants, haulm killers and, especially, as weed killers.Weeds in the broadest sense is understood to mean all plants which growin locations where they are undesired. Whether the substances accordingto the invention act as total or selective herbicides dependsessentially on the amount used.

The active compounds according to the invention can be used, forexample, in connection with the following plants:

Dicotyledonous weeds of the genera: Abutilon, Amaranthus, Ambrosia,Anoda, Anthemis, Aphanes, Atriplex, Bellis, Bidens, Capsella, Carduus,Cassia, Centaurea, Chenopodium, Cirsium, Convolvulus, Datura, Desmodium,Emex, Erysimum, Euphorbia, Galeopsis, Galinsoga, Galium, Hibiscus,Ipomoea, Kochia, Lamium, Lepidium, Lindernia, Matricaria, Mentha,Mercurialis, Mullugo, Myosotis, Papaver, Pharbitis, Plantago, Polygonum,Portulaca, Ranunculus, Raphanus, Rorippa, Rotala, Rumex, Salsola,Senecio, Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenoclea,Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola,Xanthium.

Dicotyledonous crops of the genera: Arachis, Beta, Brassica, Cucumis,Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca,Linum, Lycopersicon, Nicotiana, Phaseolus, Pisum, Solanum, Vicia.

Monocotyledonous weeds of the genera: Aegilops, Agropyron, Agrostis,Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus, Commelina,Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa, Eleocharis,Eleusine, Eragrostis, Eriochloa, Festuca, Fimbristylis, Heteranthera,Imperata, Ischaemum, Leptochloa, Lolium, Monochoria, Panicum, Paspalum,Phalaris, Phleum, Poa, Rottboellia, Sagittaria, Scirpus, Setaria,Sorghum.

Monocotyledonous crops of the izenera: Allium, Ananas, Asparagus, Avena,Hordeum, Oryza, Panicum, Saccharum, Secale, Sorghum, Triticale,Triticum, Zea.

However, the use of the active compounds according to the invention isin no way restricted to these genera, but also extends in the samemanner to other plants.

The active compounds according to the invention are suitable, dependingon the concentration, for the total control of weeds, for example onindustrial terrain and rail tracks, and on paths and squares with andwithout tree plantings. Similarly, the active compounds according to theinvention can be employed for controlling weeds in perennial crops, forexample forests, decorative tree plantings, orchards, vineyards, citrusgroves, nut orchards, banana plantations, coffee plantations, teaplantations, rubber plantations, oil palm plantations, cocoaplantations, soft fruit plantings and hop fields, on lawns, turf andpastureland, and for the selective control of weeds in annual crops.

The compounds of the formula (I) according to the invention have strongherbicidal activity and a broad spectrum of activity when applied on thesoil and to above-ground parts of plants. To a certain extent, they arealso suitable for the selective control of monocotyledonous anddicotyledonous weeds in monocotyledonous and dicotyledonous crops, bothby the pre-emergence and by the post-emergence method.

If appropriate, the compounds according to the invention can, at certainconcentrations and application rates, also be employed as microbicides,for example as fungicides, antimycotics and bactericides. Ifappropriate, they can also be used as intermediates or precursors in thesynthesis of other active compounds.

According to the invention, it is possible to treat all plants and partsof plants. Plants are to be understood here as meaning all plants andplant populations such as desired and undesired wild plants or cropplants (including naturally occurring crop plants). Crop plants can beplants which can be obtained by conventional breeding and optimizationmethods or by biotechnological and genetic engineering methods orcombinations of these methods, including the transgenic plants andincluding plant cultivars which can or cannot be protected by plantbreeders' certificates. Parts of plants are to be understood as meaningall above-ground and below-ground parts and organs of plants, such asshoot, leaf, flower and root, examples which may be mentioned beingleaves, needles, stems, trunks, flowers, fruit-bodies, fruits and seedsand also roots, tubers and rhizomes. Parts of plants also includeharvested plants and vegetative and generative propagation material, forexample seedlings, tubers, rhizomes, cuttings and seeds.

The treatment of the plants and parts of plants according to theinvention with the active compounds is carried out directly or by actionon their environment, habitat or storage area according to customarytreatment methods, for example by dipping, spraying, evaporating,atomizing, broadcasting, brushing-on and, in the case of propagationmaterial, in particular in the case of seeds, furthermore by one- ormulti-layer coating.

The active compounds can be converted to the customary formulations,such as solutions, emulsions, wettable powders, suspensions, powders,dusts, pastes, soluble powders, granules, suspension-emulsionconcentrates, natural and synthetic materials impregnated with activecompound and microencapsulations in polymeric substances.

These formulations are produced in a known manner, for example by mixingthe active compounds with extenders, that is liquid solvents, and/orsolid carriers, optionally with the use of surfactants, that isemulsifiers and/or dispersants, and/or foam-formers.

If the extender used is water, it is also possible to employ, forexample, organic solvents as auxiliary solvents. Essentially, suitableliquid solvents are: aromatics, such as xylene, toluene oralkylnaphthalenes, chlorinated aromatics or chlorinated aliphatichydrocarbons, such as chlorobenzenes, chloroethylenes or methylenechloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, forexample petroleum fractions, mineral and vegetable oils, alcohols, suchas butanol or glycol, and also their ethers and esters, ketones, such asacetone, methyl ethyl ketone, nethyl isobutyl ketone or cyclohexanone,strongly polar solvents, such as dimethylformamide and dimethylsulphoxide, and also water.

As solid carriers there are suitable:

for example ammonium salts and ground natural minerals, such as kaolins,clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceousearth, and ground synthetic minerals, such as highly disperse silica,alumina and silicates; as solid carriers for granules there aresuitable: for example crushed and fractionated natural rocks such ascalcite, marble, pumice, sepiolite and dolomite, and also syntheticgranules of inorganic and organic meals, and granules of organicmaterial such as sawdust, coconut shells, maize cobs and tobacco stalks;as emulsifiers and/or foam-formers there are suitable: for examplenonionic and anionic emulsifiers, such as polyoxyethylene fatty acidesters, polyoxyethylene fatty alcohol ethers, for example alkylarylpolyglycol ethers, alkylsulphonates, alkyl sulphates, arylsulphonatesand also protein hydrolysates; as dispersants there are suitable: forexample lignin-sulphite waste liquors and methylcellulose.

Tackifiers, such as carboxymethylcellulose and natural and syntheticpolymers in the form of powders, granules or latices, such as gumarabic, polyvinyl alcohol and polyvinyl acetate, as well as naturalphospholipids, such as cephalins and lecithins, and syntheticphospholipids, can be used in the formulations. Other additives can bemineral and vegetable oils.

It is possible to use colorants, such as inorganic pigments, for exampleiron oxide, titanium oxide and Prussian Blue, and organic dyestuffs,such as alizarin dyestuffs, azo dyestuffs and metal phthalocyaninedyestuffs, and trace nutrients, such as salts of iron, manganese, boron,copper, cobalt, molybdenum and zinc.

The formulations generally comprise between 0.1 and 95% by weight ofactive compound, preferably between 0.5 and 90%.

The active compound according to the invention can be present incommercially available formulations and in the use forms, prepared fromthese formulations, as a mixture with other active compounds, such asinsecticides, attractants, sterilizing agents, bactericides, acaricides,nematicides, fungicides, growth-regulating substances or herbicides. Theinsecticides include, for example, phosphoric acid esters, carbamates,carboxylates, chlorinated hydrocarbons, phenylureas and substancesproduced by microorganisms, inter alia.

Particularly favourable examples of co-components in mixtures are thefollowing compounds:

Fungicides

aldimorph, ampropylfos, ampropylfos potassium, andoprim, anilazine,azaconazole, azoxystrobin,

benalaxyl, benodanil, benomyl, benzamacril, benzamacryl-isobutyl,bialaphos, binapacryl, biphenyl, bitertanol, blasticidin-S,bromuconazole, bupirimate, buthiobate,

calcium polysulphide, capsimycin, captafol, captan, carbendazim,carboxin, carvon, quinomethionate, chlobenthiazone, chlorfenazole,chloroneb, chloropicrin, chlorothalonil, chlozolinate, clozylacon,cufraneb, cymoxanil, cyproconazole, cyprodinil, cyprofuram,

debacarb, dichlorophen, diclobutrazole, diclofluanid, diclomezine,dicloran, diethofencarb, difenoconazole, dimethirimol, dimethomorph,diniconazole, diniconazole-M, dinocap, diphenylamine, dipyrithione,ditalimfos, dithianon, dodemorph, dodine, drazoxolon,

edifenphos, epoxiconazole, etaconazole, ethirimol, etridiazole,

famoxadon, fenapanil, fenarimol, fenbuconazole, fenfuram, fenitropan,fenpiclonil, fenpropidin, fenpropimorph, fentin acetate, fentinhydroxide, ferbam, ferimzone, fluazinam, flumetover, fluoromide,fluquinconazole, flurprimidol, flusilazole, flusulfamide, flutolanil,flutriafol, folpet, fosetyl-aluminium, fosetyl-sodium, fthalide,fuberidazole, furalaxyl, furametpyr, furcarbonil, furconazole,furconazole-cis, furmecyclox,

guazatine,

hexachlorobenzene, hexaconazole, hymexazole,

imazalil, imnibenconazole, iminoctadine, iminoctadine albesilate,iminoctadine triacetate, iodocarb, ipconazole, iprobenfos (IBP),iprodione, irumamycin, isoprothiolane, isovaledione,

kasugamycin, kresoxim-methyl, copper preparations, such as: copperhydroxide, copper naphthenate, copper oxychloride, copper sulphate,copper oxide, oxine-copper and Bordeaux mixture,

mancopper, mancozeb, maneb, meferimzone, mepanipyrim, mepronil,metalaxyl, metconazole, methasulfocarb, methfuroxam, metiram,metomeclam, metsulfovax, mildiomycin, myclobutanil, myclozolin,

nickel dimethyidithiocarbamate, nitrothal-isopropyl, nuarimol,

ofurace, oxadixyl, oxamocarb, oxolinic acid, oxycarboxim, oxyfenthiin,

paclobutrazole, pefurazoate, penconazole, pencycuron, phosdiphen,pimaricin, piperalin, polyoxin, polyoxorim, probenazole, prochloraz,procymidone, propamocarb, propanosine-sodium, propiconazole, propineb,pyrazophos, pyrifenox, pyrimethanil, pyroquilon, pyroxyfur,

quinconazole, quintozene (PCNB),

sulphur and sulphur preparations,

tebuconazole, tecloftalam, tecnazene, tetcyclasis, tetraconazole,thiabendazole, thicyofen, thifluzamide, thiophanate-methyl, thiram,tioxymid, tolclofos-methyl, tolylfluanid, triadimefon, triadimenol,triazbutil, triazoxide, trichlatmide, tricyclazole, tridemorph,triflumizole, triforine, triticonazole,

uniconazole,

validamycin A, vinclozolin, viniconazole,

zarilamide, zineb, ziram and also

Dagger G,

OK-8705,

OK-8801,

α-(1,1-dimethylethyl)-β-(2-phenoxyethyl)-1H-1,2,4-triazole-1-ethanol,

α-(2,4-dichlorophenyl)-β-fluoro-β-propyl-1H-1,2,4-triazole-1-ethanol,

α-(2,4-dichlorophenyl)-β-methoxy-α-methyl-1H-1,2,4-triazole-1-ethanol,

α-(5-methyl-1,3-dioxan-5-yl)-β-[[4-(trifluoromethyl)-phenyl]-methylene]-1H-1,2,4-triazole-1-ethanol,

(5RS,6RS)-6-hydroxy-2,2,7,7-tetramethyl-5-(1H-1,2,4-triazol-1-yl)-3-octanone,

(E)-α-(methoxyirmino)-N-methyl-2-phenoxy-phenylacetamide,

1-isopropyl{2-methyl-1-[[[1-(4-methylphenyl)-ethyl]-amino]-carbonyl]-propyl}-carbamate,

1-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-yl)-ethanone-O-(phenylmethyl)-oxime,

1-(2-methyl-1-naphthalenyl)-1H-pyrrole-2,5-dione,

1-(3,5-dichlorophenyl)-3-(2-propenyl)-2,5-pyrrolidindione,

1-[(diiodomethyl)-sulphonyl]-4-methyl-benzene,

1-[[2-(2,4-dichlorophenyl)-1,3-dioxolan-2-yl]-methyl]-1H-imidazole,

1-[[2-(4-chlorophenyl)-3-phenyloxiranyl]-methyl]-1H-1,2,4-triazole,

1-[1-[2-[(2,4-dichlorophenyl)-methoxy]-phenyl]-ethenyl]-1H-imidazole,

1-methyl-5-nonyl-2-(phenylmethyl)-3-pyrrolidinol,

2′,6′-dibromo-2-methyl-4′-trifluoromethoxy-4′-trifluoro-methyl-1,3-thiazole-5-carboxanilide,

2,2-dichloro-N-[1-(4-chlorophenyl)-ethyl]1-ethyl-3-methyl-cyclopropanecarboxamide,

2,6-dichloro-5-(methylthio)-4-pyrimidinyl-thiocyanate,

2,6-dichloro-N-(4-trifluoromethylbenzyl)-benzamide,

2,6-dichloro-N-[[4-(trifluoromethyl)-phenyl]-methyl]-benzamide,

2-(2,3,3-triiodo-2-propenyl)-2H-tetrazole,

2-[(1-methylethyl)-sulphonyl]-5-(trichloromethyl)-1,3,4-thiadiazole,

2-[[6-deoxy-4-O-(4-O-methyl-β-D-glycopyranosyl)-α-D-glucopyranosyl]-amino]4-methoxy-1H-pyrrolo[2,3-d]pyrinidine-5-carbonitrile,

2-aminobutane,

2-bromo-2-(bromomethyl)-pentanedinitrile,

2-chloro-N-(2,3-dihydro-1,1,3-trimethyl-1H-inden-4-yl)-3-pyridinecarboxamide,

2-chloro-N-(2,6-dimethylphenyl)-N-(isothiocyanatomethyl)-acetamide,

2-phenylphenol (OPP),

3,4-dichloro-1-[4-(difluoromethoxy)-phenyl]-1H-pyrrole-2,5-dione,

3,5-dichloro-N-[cyano[(1-methyl-2-propynyl)-oxy]-methyl]-benzamide,

3-(1,1-dimethylpropyl-1-oxo-1H-indene-2-carbonitrile,

3-[2-(4-chlorophenyl)-5-ethoxy-3-isoxazolidinyl]-pynidine,

4-chloro-2-cyano-N,N-dimethyl-5-(4-methylphenyl)-1H-imidazole-1-sulphonamide,

4-methyl-tetrazolo[1,5-a]quinazolin-5(4H)-one,

8-(1,1-dimethylethyl)-N-ethyl-N-propyl-1,4-dioxaspiro[4.5]decane-2-methanamine,

8-hydroxyquinoline sulphate,

9H-xanthene-2-[(phenylamino)-carbonyl]-9-carboxylic hydrazide,

bis-(1-methylethyl)-3-methyl-4-[(3-methylbenzoyl)-oxy]-2,5-thiophenedicarboxylate,

cis-1-(4-chlorophenyl)-2-(1H-1,2,4-triazol-1-yl)-cycloheptanol,

cis-4-[3-[4-(1,1-dimethylpropyl)-phenyl-2-methylpropyl]-2,6-dimethyl-morpholinehydrochloride,

ethyl [(4-chlorophenyl)-azo]-cyanoacetate,

potassium bicarbonate,

methanetetrathiol-sodium salt,

methyl1-(2,3-dihydro-2,2-dimethyl-1H-inden-1-yl)-1H-imidazole-5-carboxylate,

methyl N-(2,6-dimethylphenyl)-N-(5-isoxazolylcarbonyl)-DL-alaninate,

methyl N-(chloroacetyl)-N-(2,6-dimethylphenyl)-DL-alaninate,

N-(2,3-dichloro-4-hydroxyphenyl)-1-methyl-cyclohexanecarboxamide,

N-(2,6-dimethylphenyl)-2-methoxy-N-(tetrahydro-2-oxo-3-furanyl)-acetanide,

N-(2,6-dimethylphenyl)-2-methoxy-N-(tetrahydro-2-oxo-3-thienyl)-acetamide,

N-(2-chloro-4-nitrophenyl)-4-methyl-3-nitro-benzenesulphonamide,

N-(4-cyclohexylphenyl)-1,4,5,6-tetrahydro-2-pyrimidinarnine,

N-(4-hexylphenyl)-1,4,5,6-tetrahydro-2-pyrimidinamine,

N-(5-chloro-2-methylphenyl)-2-methoxy-N-(2-oxo-3-oxazolidinyl)-acetamide,

N-((6-methoxy)-3-pyridinyl)-cyclopropanecarboxamide,

N-[2,2,2-trichloro-1-[(chloroacetyl)-amino]-ethyl]-benzamide,

N-[3-chloro-4,5-bis-(2-propinyloxy)-phenyl]-N′-methoxy-methanimidamide,

N-formyl-N-hydroxy-DL-alanine-sodium salt,

O,O-diethyl [2-(dipropylamino)-2-oxoethyl]-ethylphosphorarnidothioate,

O-methyl S-phenyl phenylpropylphosphoramidothioate,

S-methyl 1,2,3-benzothiadiazole-7-carbothioate,

spiro[2H]-1-benzopyrane-2,1′(3′H)-isobenzofuran]-3′-one,

Bactericides

bronopol, dichlorophen, nitrapyrin, nickel dimethyldithiocarbamate,kasugamycin, octhilinone, furancarboxylic acid, oxytetracyclin,probenazole, streptomycin, tecloftalam, copper sulphate and other copperpreparations.

Insecticides/Acaricides/Nematicides

abamectin, acephate, acetamiprid, acrinathrin, alanycarb, aldicarb,aldoxycarb, alphacypermethrin, alphamethrin, arnitraz, avermectin, AZ60541, azadirachtin, azamethiphos, azinphos A, azinphos M, azocyclotin,

Bacillus popilliae, Bacillus sphaericus, Bacillus subtilis, Bacillusthuringiensis, baculoviruses, Beauveria bassiana, Beauveria tenella,bendiocarb, benfuracarb, bensultap, benzoximate, betacyfluthrin,bifenazate, bifenthrin, bioethanomethrin, biopermethrin, BPMC, bromophosA, bufencarb, buprofezin, butathiofos, butocarboxim, butylpyridaben,

cadusafos, carbaryl, carbofuran, carbophenothion, carbosulfan, cartap,chloethocarb, chlorethoxyfos, chlorfenapyr, chlorfenvinphos,chlorfluazuron, chlormephos, chlorpyrifos, chlorpyrifos M,chlovaporthrin, cis-resmethrin, cispermethrin, clocythrin, cloethocarb,clofentezine, cyanophos, cycloprene, cycloprothrin, cyfluthrin,cyhalothrin, cyhexatin, cypennethrin, cyromazine,

deltamethrin, demeton M, demeton S, demeton-S-methyl, diafenthiuron,diazinon, dichlorvos, diflubenzuron, dimethoate, dimethylvinphos,diofenolan, disulfoton, docusat-sodium, dofenapyn,

eflusilanate, emamectin, empenthrin, endosulfan, Entomopfthora spp.,esfenvalerate, ethiofencarb, ethion, ethoprophos, etofenprox, etoxazole,etrimfos,

fenamiphos, fenazaquin, fenbutatin oxide, fenitrothion, fenothiocarb,fenoxacrim, fenoxycarb, fenpropathrin, fenpyrad, fenpyrithrin,fenpyroximate, fenvalerate, fipronil, fluazinam, fluazuron,flubrocythrinate, flucycloxuron, flucythrinate, flufenoxuron,flutenzine, fluvalinate, fonophos, fosmethilan, fosthiazate, fubfenprox,furathiocarb,

granulosis viruses,

halofenozide, HCH, heptenophos, hexaflumuron, hexythiazox, hydroprene,

imidacloprid, isazofos, isofenphos, isoxathion, ivermectin,

nuclear polyhedrosis viruses,

lambda-cyhalothrin, lufenuron,

malathion, mecarbam, metaldehyde, methamidophos, Metharhiziumanisopliae, Metharhizium flavoviride, methidathion, methiocarb,methomyl, methoxyfenozide, metolcarb, metoxadiazone, mevinphos,milbemectin, monocrotophos,

naled, nitenpyram, nithiazine, novaluron,

omethoate, oxamyl, oxydemethon M,

Paecilomyces fumosoroseus, parathion A, parathion M, pernethrin,phenthoate, phorate, phosalone, phosmet, phosphamidon, phoxim,pirimicarb, pirimiphos A, pirimiphos M, profenofos, promecarb, propoxur,prothiofos, prothoate, pymetrozine, pyraclofos, pyresmethrin, pyrethrum,pyridaben, pyridathion, pyrimidifen, pyri-proxyfen,

quinalphos,

ribavirin,

salithion, sebufos, silafluofen, spinosad, sulfotep, sulprofos,

tau-fluvalinate, tebufenozide, tebufenpyrad, tebupirimiphos,teflubenzuron, tefluthrin, temephos, temivinphos, terbufos,tetrachlorvinphos, theta-cypennethrin, thiamethoxam, thiapronil,thiatriphos, thiocyclam hydrogen oxalate, thiodicarb, thiofanox,thuringiensin, tralocythrin, tralomethrin, triarathene, triazamate,triazophos, triazuron, trichlophenidine, trichlorfon, triflumuron,trimethacarb,

vamidothion, vaniliprole, Verticillium lecanii,

YI5302,

zeta-cypermethrin, zolaprofos,

(1R-cis)-[5-(phenylmethyl)-3-furanyl]-methyl-3-[(dihydro-2-oxo-3(2H)-furanylidene)-methyl]-2,2-dimethylcyclopropanecarboxylate,

(3-phenoxyphenyl)-methyl-2,2,3,3-tetramethylcyclopropanecarboxylate,

1-[(2-chloro-5-thiazolyl)methyl]tetrahydro-3,5-dimethyl-N-nitro-1,3,5-triazine-2(1H)-imine,

2-(2-chloro-6-fluorophenyl)-4-[4-(1,1-dimethylethyl)phenyl]-4,5-dihydro-oxazole,

2-(acetyloxy)-3-dodecyl-1,4-naphthalenedione,

2-chloro-N-[[[4-(1-phenylethoxy)-phenyl]-amino]-carbonyl]-benzamide,

2-chloro-N-[[[4-(2,2-dichloro-1,1-difluoroethoxy)-phenyl]-amino]-carbonyl]-benzamide,

3-methylphenyl propylcarbamate,

4-[4-(4-ethoxyphenyl)-4-methylpentyl]-1-fluoro-2-phenoxy-benzene,

4-chloro-2-(1,1-dimethylethyl)-5-[[2-(2,6-dimethyl-4-phenoxyphenoxy)ethyl]thio]-3(2H)-pyridazinone,

4-chloro-2-(2-chloro-2-methylpropyl)-5-[(6-iodo-3-pyridinyl)methoxy]-3(2H)-pyridazinone,

4-chloro-5-[(6-chloro-3-pyridinyl)methoxy]-2-(3,4-dichlorophenyl)-3(2H)-pyridazinone,

Bacillus thuringiensis strain EG-2348,

2-benzoyl-1-(1,1-dimethylethyl)-hydrazinobenzoic acid,

2,2-dimethyl-3-(2,4-dichlorophenyl)-2-oxo-1-oxaspiro[4.5]dec-3-en-4-ylbutanoate,

[3-[(6-chloro-3-pyridinyl)methyl]-2-thiazolidinylidene]-cyanamide,

dihydro-2-(nitromethylene)-2H-1,3-thiazine-3(4H)-carboxaldehyde,

ethyl[2-[[1,6-dihydro-6-oxo-1-(phenylmethyl)-4-pyridazinyl]oxy]ethyl]-carbamate,

N-(3,4,4-trifluoro-1-oxo-3-butenyl)-glycine,

N-(4-chlorophenyl)-3-[4-(difluoromethoxy)phenyl]-4,5-dihydro-4-phenyl-1H-pyrazole-1-carboxamide,

N-[(2-chloro-5-thiazolyl)methyl]-N′-methyl-N″-nitro-guanidine,

N-methyl-N′-(1-methyl -2-propenyl)-1,2-hydrazinedicarbothioamide,

N-methyl-N′-2-propenyl-1,2-hydrazinedicarbothioamide,

O,O-diethyl [2-(dipropylamino)-2-oxoethyl]-ethylphosphoramidothioate.

For controlling weeds, the active compounds according to the invention,as such or in their formulations, can also be used as mixtures withknown herbicides and/or substances which improve the compatibility withcrop plants (“safeners”), finished formulations or tank mixes beingpossible. Also possible are mixtures with weed-killers comprising one ormore known herbicides and a safener.

Possible components for the mixtures are known herbicides, for example

acetochlor, acifluorfen (-sodium), aclonifen, alachlor, alloxydim(-sodium), ametryne, amicarbazone, amidochlor, amidosulfuron, anilofos,asulam, atrazine, azafenidin, azimsulfuron, BAS-662H, beflubutamid,benazolin (-ethyl), benfuresate, bensulfuron (-methyl), bentazon,benzfendizone, benzobicyclon, benzofenap, benzoylprop (-ethyl),bialaphos, bifenox, bispyribac (-sodium), bromobutide, bromofenoxim,bromoxynil, butachlor, butafenacil (-allyl), butroxydim, butylate,cafen-strole, caloxydim, carbetamide, carfentrazone (-ethyl),chlomethoxyfen, chloramben, chloridazon, chlorimuron (-ethyl),chlornitrofen, chlorsulfuron, chlortoluron, cinidon (-ethyl),cinmethylin, cinosulfuron, clefoxydim, clethodim, clodinafop(-propargyl), clomazone, clomeprop, clopyralid, clopyrasulfuron(-methyl), cloransulam (-methyl), cumyluron, cyanazine, cybutryne,cycloate, cyclosulfamuron, cycloxydim, cyhalofop (-butyl), 2,4-D,2,4-DB, desmedipham, diallate, dicamba, dichlorprop (-P), diclofop(-methyl), diclosulam, diethatyl (-ethyl), difenzoquat, diflufenican,diflufenzopyr, dimefuron, dimepiperate, dimethachlor, dimethametryn,dimethenamid, dimexyflam, dinitramine, diphenamid, diquat, dithiopyr,diuron, dymron, epropodan, EPTC, esprocarb, ethalfluralin,ethametsulfuron (-methyl), ethofumesate, ethoxyfen, ethoxy-sulfuron,etobenzanid, fenoxaprop (-P-ethyl), fentrazamide, flamprop (-isopropyl,-isopropyl-L, -methyl), flazasulfuron, florasulam, fluazifop (-P-butyl),fluazolate, flucarbazone (-sodium), flufenacet, flumetsulam, flumiclorac(-pentyl), flumioxazin, flumipropyn, flumetsulam, fluometuron,fluorochloridone, fluoroglycofen (-ethyl), flupoxam, flupropacil,flurpyrsulfuron (-methyl, -sodium), flurenol (-butyl), fluridone,fluroxypyr (-butoxypropyl, -meptyl), flurprimidol, flurtamone,fluthiacet (-methyl), fluthiamide, fomesafen, foramsulfuron, glufosinate(-ammonium), glyphosate (-isopropylammonium), halosafen, haloxyfop(-ethoxyethyl, -P-methyl), hexazinone, imazamethabenz (-methyl),imazamethapyr, imazamox, imazapic, imazapyr, imazaquin, imazethapyr,imazosulfuron, iodosulfuron (-methyl, -sodium), ioxynil, isopropalin,isoproturon, isouron, isoxaben, isoxachlortole, isoxaflutole,isoxapyrifop, lactofen, lenacil, linuron, MCPA, mecoprop, mefenacet,mesotrione, metamitron, metazachlor, methabenzthiazuron, metobenzuron,metobromuron, (alpha-) metolachlor, metosulam, metoxuron, metribuzin,metsulfuron (-methyl), molinate, monolinuron, naproanilide, napropamide,neburon, nicosulfuron, norflurazon, orbencarb, oryzalin, oxadiargyl,oxadiazon, oxasulfuron, oxaziclomefone, oxyfluorfen, paraquat,pelargonic acid, pendimethalin, pendralin, pentoxazone, phenmedipham,picolinafen, piperophos, pretilachlor, primisulfuron (-methyl),profluazol, prometryn, propachlor, propanil, propaquizafop,propisochlor, propoxycarbazone (-sodium), propyzamide, prosulfocarb,prosulfuron, pyraflufen (-ethyl), pyrazogyl, pyrazolate, pyrazosulfuron(-ethyl), pyrazoxyfen, pyribenzoxim, pyributicarb, pyridate, pyridatol,pyriftalid, pyriminobac (-methyl), pyrithiobac (-sodium), quinchlorac,quinmerac, quinoclamine, quizalofop (-P-ethyl, -P-tefuryl), rimsulfuron,sethoxydim, simazine, simetryn, sulcotrione, sulfentrazone, sulfometuron(-methyl), sulfosate, sulfosulfuron, tebutam, tebuthiuron, tepraloxydim,terbuthylazine, terbutryn, thenylchlor, thiafluamide, thiazopyr,thidiazimin, thifensulfuron (-methyl), thiobencarb, tiocarbazil,tralkoxydim, triallate, triasulfuron, tribenuron (-methyl), triclopyr,tridiphane, trifluralin, trifloxysulfuron, triflusulfuron (-methyl),tritosulfuron.

When used as insecticides, the active compounds according to theinvention can furthermore be present in their commercially availableformulations and in the use forms, prepared from these formulations, asa mixture with synergistic agents. Synergistic agents are compoundswhich increase the action of the active compounds, without it beingnecessary for the synergistic agent added to be active itself.

The active compound content of the use forms prepared from thecommercially available formulations can vary within wide limits. Theactive compound concentration of the use forms can be from 0.0000001 to95% by weight of active compound, preferably between 0.0001 and 1% byweight.

The compounds are employed in a customary manner appropriate for the useforms.

When used against hygiene pests and pests of stored products, the activecompound is distinguished by an excellent residual action on wood andclay as well as a good stability to alkali on limed substrates.

When used as herbicides, the active compounds can be applied as such, inthe form of their formulations or of the use forms prepared therefrom byfurther dilution, such as ready-to-use solutions, suspensions,emulsions, powders, pastes and granules. Application is carried out in acustomary manner, for example by watering, spraying, atomizing,broadcasting.

The active compounds according to the invention can be applied before orafter emergence of the plants. They can also be incorporated into thesoil prior to sowing.

The application rate used can vary within a relatively wide range.Essentially, it depends on the kind of effect desired. In general, theapplication rates are between 1 g and 10 kg of active compound perhectare of soil surface, preferably between 5 g and 5 kg per ha.

Having low toxicity to warm-blooded animals, the active compounds of theformula (I) are also suitable for controlling pathogenic endoparasitesand ectoparasites which occur in humans and in animal keeping and animalbreeding, in productive animals, breeding animals, zoo animals,laboratory animals, animals for experimentation and pets. They areactive against all or individual stages of development of the pests andagain resistant and normally sensitive species. By controlling thepathogenic parasites it is intended to reduce disease, mortality andreductions in yield (for example in the production of meat, milk, wool,hides, eggs, honey, etc.), so that the use of the active compoundsenables more economical and simpler animal keeping. The pathogenicendoparasites include cestodes, trematodes, nematodes; the ectoparasitesinclude arthropods, preferably insects and arachnids.

The following endoparasites may be mentioned in particular:

From the order of the Pseudophyllidea, for example: Diphyllobothriumspp., Spirometra spp., Schistocephalus spp., Ligula spp., Bothridiumspp., Diphlogonoporus spp.

From the order of the Cyclophyllidea, for example: Mesocestoides spp.,Anoplocephala spp., Paranoplocephala spp., Moniezia spp., Thysanosomsaspp., Thysaniezia spp., Avitellina spp., Stilesia spp., Cittotaeniaspp., Anhyra spp., Bertiella spp., Taenia spp., Echinococcus spp.,Hydratigera spp., Davainea spp., Raillietina spp., Hymenolepsis spp.,Echinolepsis spp., Echinocotyle spp., Diorchis spp., Dipylidium spp.,Joyeuxiella spp., Diplopylidium spp.

From the sub-class of the Monogenea, for example: Cyrodactylus spp.,Dactylogyrus spp., Polystoma spp.

From the sub-class of the Digenea, for example: Diplostomum spp.,Posthodiplostomum spp., Schistosoma spp., Trichobilharzia spp.,Omithobilharzia spp., Austrobilharzia spp., Gigantobilharzia spp.,Leucochloridium spp., Brachylaima spp., Echinostoma spp.,Echinoparyphium spp., Echinochasmus spp., Hypoderaeum spp., Fasciolaspp., Fasciolides spp., Fasciolopsis spp., Cyclocoelum spp.,Typhloccelum spp., Paramphistomum spp., Calicophoron spp., Cotylophoronspp., Gigantocotyle spp., Fischoederius spp., Gastrothylacus spp.,Notocotylus spp., Catatropis spp., Plagiorchis spp., Prosthogonismusspp., Dicrocoelium spp., Collyriclum spp., Nanophyetus spp.,Opisthorchis spp., Clonorchis spp., Metorchis spp., Heterophyes spp.,Metagonimus spp.

From the order of the Enoplida, for example: Trichuris spp., Capillariaspp., Trichlomosoides spp., Trichinella spp.

From the order of the Rhabditia, for example: Micronema spp.,Strongyloides spp.

From the order of the Strongylida, for example: Stronylus spp.,Triodontophorus spp., Oesophagodontus spp., Trichonema spp.,Gyalocephalus spp., Cylindropharynx spp., Poteriostromum spp.,Cyclococercus spp., Cylicostephanus spp., Oesophagostomum spp.,Chabertia spp., Stephanurus spp., Acylostoma spp., Uncinaria spp.,Bunostomum spp., Globocephalus spp., Syngamus spp., Cyathostoma spp.,Metastrongylus spp., Dictyocaulus spp., Muellerius spp., Protostrongylusspp., Neostrongylus spp., Cystocaulus spp., Pneumostrongyius spp.,Spicocaulus spp., Elaphostrongylus spp., Parelaphostrongylus spp.,Crenosoma spp., Paracrenosoma spp., Angiostrongylus spp.,Aelurostrongylus spp., Filaroides spp., Parafilaroides spp.,Trichostrongylus spp., Haemonchus spp., Ostertagia spp., Marshallagiaspp., Cooperia spp., Nematodirus spp., Hyostrongylus spp., Obeliscoidesspp., Amidostomum spp., Ollulanus spp.

From the order of the Oxyurida, for example: Oxyuris spp., Enterobiusspp., Passalurus spp., Syphacia spp., Aspiculuris spp., Heterakis spp.

From the order of the Ascaridia, for example: Ascaris spp., Toxascarisspp., Toxocara spp., Parascaris spp., Anisakis spp., Ascaridia spp.

From the order of the Spirurida, for example: Gnathostoma spp.,Physaloptera spp., Thelazia spp., Gongylonema spp., Habronema spp.,Parabronema spp., Draschia spp., Dracunculus spp.

From the order of the Filariida, for example: Stephanofilaria spp.,Parafilaria spp., Setaria spp., Loa spp., dirofilaria spp., Litomosoidesspp., Brugia spp., Wuchereria spp., Onchocerca spp.

From the group of the Gigantohynchida, for example: Filicollis spp.,Moniliformis spp., Macracanthorhynchus spp., Prosthenorchis spp.

The ectoparasites include, in particular:

From the order of the Anoplura, for example, Haematopinus spp.,Linognathus spp., Solenopotes spp., Pediculus spp., Pthirus spp.;

From the order of the Mallophaga, for example, Trimenopon spp., Menoponspp., Eomenacanthus spp., Menacanthus spp., Trichodectes spp., Felicolaspp., Damalinea spp., Bobiola spp.;

From the order of the Diptera, for example, Chrysops spp., Tabanus spp.,Musca spp., Hydrotaea spp., Muscina spp., Haematobosca spp., Haematobiaspp., Stomoxys spp., Fannia spp., Glossina spp., Lucilia spp.,Calliphora spp., Auchmeromyia spp., Cardylobia spp., Cochiomyia spp.,Chrysomyia spp., Sarcophaga spp., Wohlfartia spp., Gaserophilus spp.,Oesteromyia spp., Oedemagena spp., Hyporma spp., Oestrus spp.,Rhinoestrus spp., Melophagus spp., Hippobosca spp.

From the order of the Siphonaptera, for example, Ctenocephalides spp.,Echidnophaga spp., Ceratophyllus spp.

From the order of the Metastigmata, for example, Hyalomma spp.,Rhipicephalus spp., Boophilus spp., Amblyomma spp., Haemophysalis spp.,Dermacentor spp., Ixodes spp., Argas spp., Ornithodorus spp., Otobiusspp.;

From the order of the Mesastigmata, for example, Dermanyssus spp.,Ornithonyssus spp., Pneumonyssus spp.

From the order of the Prostigmata, for example, Cheyletiella spp.,Psorergates spp., Myobia spp., Demdex spp., Neotrombicula spp.;

From the order of the Astigmata, for example, Acarus spp., Myocoptesspp., Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp.,Notoedres spp., Knemidocoptes spp., Neoknemidodoptex spp., Lytoditesspp., Laminosioptes spp.

The productive and breeding animals include mammals, such as, forexample, cattle, horses, sheep, pigs, goats, camels, water buffalo,donkeys, rabbits, fallow deer and reindeer, fur-bearing animals, suchas, for example, mink, chinchilla and raccoon, birds, such as, forexample, hens, geese, turkeys and ducks, fresh- and salt-water fish,such as, for example, trout, carp and eels, reptiles, insects, such as,for example, honey-bee and silkworm.

Laboratory and experimental animals include, for example, mice, rats,guinea-pigs, golden hamsters, dogs and cats.

The pets include, for example, dogs and cats.

Administration can be effected prophylactically as well astherapeutically.

The active compounds are administered, either directly or in the form ofsuitable preparations, enterally, parenterally, dermally, nasally, bytreating the habitat or with the aid of shaped articles containing theactive comopund, such as, for example, strips, plates, tapes, collars,ear tags, limb bands or marking devices.

Enteral administration of the active compounds is effected, for example,orally in the form of powders, tablets, capsules, pastes, boluses,drenches, granules, of solutions, suspensions or emulsions which can beapplied orally, of medicated feed or drinking water. Dermal applicationis effected, for example, in the form of dipping, spryaing or pouring-onand spotting-on and powdering-on. Parenteral administration is effected,for example, in the form of injection (intramuscularly, subcutaneously,intravenously or intraperitoneally) or by implants.

Particular emphasis is given to the preparations for dermal application.These include solutions, suspension concentrates and emulsionconcentrates and microemulsions which are diluted with water prior touse, pour-on and spot-on formulations, powders and dusts, aerosols andshaped articles containing the active compound, and also dust-bags andback-rubbers.

These preparations are produced in a known manner, for example by mixingthe active compound with extenders, i.e. liquid solvents, if appropriateusing surfactants, i.e. emulsifiers and/or dispersants. If the extenderused is water, it is also possible to use, for example, organic solventsas auxiliary solvents.

In addition to water, the liquid diluents include alcohols, such asmethanol, ethanol, isopropanol, n-butanol, amyl alcohol, octanol;

glycols, such as propylene glycol, 1,3-butylene glycol, ethyl glycol,dipropylene glycol monomethyl ether;

glycerol;

aromatic alcohols, such as benzyl alcohol;

carboxylic esters, such as, for example, ethyl acetate, benzyl benzoate,butyl acetate, propylene carbonate, ethyl lactate;

aliphatic hydrocarbons, such as paraffins, cyclohexane, methylenechloride, ethylene chloride;

aromatic hydrocarbons, such as xylene, toluene, alkyl naphthalenes,chlorobenzenes;

ketones, such as, for example, acetone and methyl ethyl ketone, methylisobutyl ketone, cyclohexanone;

natural and synthetic mono- and triglycerides having natural fattyacids, such as cottonseed oil, peanut oil, maize germ oil, olive oil,castor oil, sesame oil;

furthermore, dimethyl sulphoxide, dimethylacetamide, dimethylformamide,N-methylpyrrolidone, dioxane, 2,2-dimethyl-4-oxymethyl-1,3-dioxolane.

The surfactants include:

emulsifiers and wetting agents, such as anionic surfactants, for examplealkylsulphonates, alkyl sulphates, arylsulphonates, Na lauryl sulphates,fatty alcohol ether sulphates, mono/dialkyl polyglycol etherorthophoshoric ester monoethanolamine salt, calcium alkylarylsulphonate;

cationic surfactants, for example cetyltrimethylammonium chloride;

ampholytic surfactants, for example di-NaN-lauryl-beta-iminodipropionate or lecithin;

nonionic surfactants, for example polyethoxylated castor oil,polyethoxylated sorbitan monooleate, polyethoxylated sorbitanmonostearate, glycerol monostearate, polyoxyethylene stearate,alkylphenol polyglycol ethers, polyethoxylated sorbitan monopalmitate,polyoxyethylene lauryl ether, polyoxyethylene oleyl ether,polyoxyethylene mannitan monolaurate, alkyl polyglycol ether, oleylpolyglycol ether, dodecyl polyglycol ether, ethoxylated nonylphenol,isooctylphenol polyethoxy ethanol.

The preparations may furthermore comprise:

tackifiers, for example carboxymethylcellulose, methylcellulose andother cellulose and starch derivatives, polyacrylates, alginates,gelatin, gum arabic, polyvinylpyrro-lidone, polyvinyl alcohol,copolymers of methyl vinyl ether and maleic anhydride, polyethyleneglycols, paraffins, oils, waxes, hydrogenated castor oil, lecithins andsynthetic phospholipids.

The preparations may comprise colorants, such as inorganic pigments, forexample iron oxide, titanium oxide, Prussian Blue, and organic dyes,such as alizarine, azo and metal phthalocyanine dyes.

The preparations may comprise spreading agents, for example siliconeoils of various viscosity, fatty acid esters, such as ethyl stearate,di-n-butyl-adipate, hexyl laurate, di-propylene glycol pelargonate,esters of a branched fatty acid of medium chain length with saturatedfatty alcohols of chain length C₁₆-C₁₈, isopropyl myristate, isopropylpalmitate, caprylic/capric acid esters of saturated fatty alcohols ofchain length C₁₂-C₁₈, isopropyl stearate, oleyl oleate, decyl oleate,ethyl oleate, ethyl lactate, waxy fatty acid esters, dibutyl phthalate,diisopropyl adipate, ester mixtures related to the latter, inter alia;

triglycerides, such as caprylic/capric triglyceride, triglyceridemixtures with plant fatty acids of chain length C₈-C₁₂ or otherspecifically selected natural fatty acids, partial glyceride mixtures ofsaturated or unsaturated, if appropriate also hydroxyl-group-containing,fatty acids, monodiglycerides of the C₈-C₁₀-fatty acids and others;

fatty alcohols, such as isotridecyl alcohol, 2-octyldodecanol,cetylstearyl alcohol, oleyl alcohol.

To prepare solid preparations, the active compound is mixed withsuitable carriers, if appropriate with addition of auxiliaries, andbrought into the desired form.

Carriers which may be mentioned are all physiologically acceptable solidinert substances. These are inorganic and organic substances. Inorganicsubstances are optionally crushed and fractionated, for examplesynthetic and natural rock meals, such as kaolins, talc, chalk, quartz,diatomaceous earth, sodium chloride, carbonates, such as calciumcarbonate, bicarbonates, aluminium oxides, silicic acids, alumina,precipitated or colloidal silica, phosphates.

Organic substances are, for example, sugar, cellulose, foodstuffs andfeeds, such as milk powder, animal meal, grain meals and shreds,starches, sawdust.

Auxiliaries are preservatives, antioxidants, colorants which havealready been mentioned above.

Other suitable auxiliaries are lubricants and glidants, such as, forexample, magnesium stearate, stearic acid, talc, bentonites,disintegration-promoting substances, such as starch or crosslinkedpolyvinylpyrrolidone, binders, such as, for example, starch, gelatin orlinear polyvinylpyrrolidone, and dry binders, such as microcrystallinecellulose.

The active compounds can be present in their abovementioned solid orliquid formulations, also in encapsulated form.

The active compounds can also be used in the form of an aerosol. To thisend, the active compound, in a suitable formulation, is finelydistributed under pressure.

It may also be advantageous to use the active compounds in formulationswhich release the active compound in a delayed manner. Examples whichmay be mentioned are shaped articles containing the active compound,such as, for example, plates, tapes, strips, collars, ear tags, tailtags, limb bands, halters, marking devices. Other examples areactive-compound-containing implants and boluses.

The active compounds can also be administered together with the feedand/or the drinking water.

In its preparations, and in the use forms prepared from thesepreparations, the active compound according to the invention can bepresent in a mixture with other active compounds, such as insecticides,sterilants, bactericides, acaricides, nematicides or fungicides. Theinsecticides include, for example, phosphoric acid esters, carbamates,carboxylic acid esters, chlorinated hydrocarbons, phenylureas,nicotinyls, neonicotinyls, substances produced by microorganisms, etc.

It has furthermore been found that the active compounds according to theinvention also have a strong insecticidal action against insects whichdestroy industrial materials.

The following insects may be mentioned as examples and as preferred—butwithout a limitation:

Beetles, such as

Hylotrupes bajulus, Chlorophorus pilosis, Anobium punctatum, Xestobiumrufovillosum, Ptilinus pecticornis, Dendrobium pertinex, Ernobiusmollis, Priobium carpini, Lyctus brunneus, Lyctus africanus, Lyctusplanicollis, Lyctus linearis, Lyctus pubescens, Trogoxylon aequale,Minthes rugicollis, Xyleborus spec., Tryptodendron spec., Apatemonachus, Bostrychus capucins, Heterobostrychus brunneus, Sinoxylonspec., Dinoderus minutus.

Hymenopterons, such as

Sirex juvencus, Urocerus gigas, Urocerus gigas taignus, Urocerus augur.

Termites, such as

Kalotermes flavicollis, Cryptotermes brevis, Heterotermes indicola,Reticulitermes flavipes, Reticulitermes santonensis, Reticulitermeslucifugus, Mastotermes darwiniensis, Zootermopsis nevadensis,Coptotermes formosanus.

Bristletails, such as Lepisma saccarina.

Industrial materials in the present connection are to be understood asmeaning non-living materials, such as, preferably, plastics, adhesives,sizes, papers and cards, leather, wood and processed wood products andcoating compositions.

Wood and processed wood products are materials to be protected,especially preferably, from insect infestation.

Wood and processed wood products which can be protected by the agentaccording to the invention or mixtures comprising this are to beunderstood as meaning, for example:

building timber, wooden beams, railway sleepers, bridge components, boatjetties, wooden vehicles, boxes, pallets, containers, telegraph poles,wood panelling, wooden windows and doors, plywood, chipboard, joinery orwooden products which are used quite generally in house-building or inbuilding joinery.

The active compounds can be used as such, in the form of concentrates orin generally customary formulations, such as powders, granules,solutions, suspensions, emulsions or pastes.

The formulations mentioned can be prepared in a manner known per se, forexample by mixing the active compounds with at least one solvent ordiluent, emulsifier, dispersing agent and/or binder or fixing agent, awater repellent, if appropriate siccatives and UV stabilizers and, ifappropriate, dyestuffs and pigments, and also other processingauxiliaries.

The insecticidal compositions or concentrates used for the preservationof wood and wood-derived timber products comprise the active compoundaccording to the invention in a concentration of 0.0001 to 95% byweight, in particular 0.001 to 60% by weight.

The amount of the compositions or concentrates employed depends on thenature and occurrence of the insects and on the medium. The optimumamount employed can be determined for the use in each case by a seriesof tests. In general, however, it is sufficient to employ 0.0001 to 20%by weight, preferably 0.001 to 10% by weight, of the active compound,based on the material to be preserved.

Solvents and/or diluents which are used are an organic chemical solventor solvent mixture and/or an oily or oil-like organic chemical solventor solvent mixture of low volatility and/or a polar organic chemicalsolvent or solvent mixture and/or water, and if appropriate anemulsifier and/or wetting agent.

Organic chemical solvents which are preferably used are oily or oil-likesolvents having an evaporation number above 35 and a flashpoint above30° C., preferably above 45° C. Substances which are used as such oilyor oil-like water-insoluble solvents of low volatility are appropriatemineral oils or aromatic fractions thereof, or solvent mixturescontaining mineral oils, preferably white spirit, petroleum and/oralkylbenzene.

Mineral oils having a boiling range from 170 to 220° C., white spirithaving a boiling range from 170 to 220° C., spindle oil having a boilingrange from 250 to 350° C., petroleum and aromatics having a boilingrange from 160 to 280° C., turpentine oil and the like, areadvantageously employed.

In a preferred embodiment, liquid aliphatic hydrocarbons having aboiling range from 180 to 210° C. or high-boiling mixtures of aromaticand aliphatic hydrocarbons having a boiling range from 180 to 220° C.and/or spindle oil and/or monochloronaphthalene, preferablyα-monochloronaphthalene, are used.

The organic oily or oil-like solvents of low volatility which have anevaporation number above 35 and a flashpoint above 30° C., preferablyabove 45° C., can be replaced in part by organic chemical solvents ofhigh or medium volatility, with the proviso that the solvent mixturelikewise has an evaporation number above 35 and a flashpoint above 30°C., preferably above 45° C., and that the insecticide/fungicide mixtureis soluble or emulsifiable in this solvent mixture.

According to a preferred embodiment, some of the organic chemicalsolvent or solvent mixture is replaced by an aliphatic polar organicchemical solvent or solvent mixture. Aliphatic organic chemical solventscontaining hydroxyl and/or ester and/or ether groups, such as, forexample, glycol ethers, esters or the like, are preferably used.

Organic chemical binders which are used in the context of the presentinvention are the synthetic resins and/or binding drying oils which areknown per se, are water-dilutable and/or are soluble or dispersible oremulsifiable in the organic chemical solvents employed, in particularbinders consisting of or comprising an acrylate resin, a vinyl resin,for example polyvinyl acetate, polyester resin, polycondensation orpolyaddition resin, polyurethane resin, alkyd resin or modified alkydresin, phenolic resin, hydrocarbon resin, such as indene-cumarone resin,silicone resin, drying vegetable oils and/or drying oils and/orphysically drying binders based on a natural and/or synthetic resin.

The synthetic resin used as the binder can be employed in the form of anemulsion, dispersion or solution. Bitumen or bituminous substances canalso be used as binders in an amount of up to 10% by weight. Dyestuffs,pigments, water-repelling agents, odour correctants and inhibitors oranticorrosive agents and the like which are known per se canadditionally be employed.

It is preferred according to the invention for the composition orconcentrate to comprise, as the organic chemical binder, at least onealkyd resin or modified alkyd resin and/or one drying vegetable oil.Alkyd resins having an oil content of more than 45% by weight,preferably 50 to 68% by weight, are preferably used according to theinvention.

All or some of the binder mentioned can be replaced by a fixing agent(mixture) or a plasticizer (mixture). These additives are intended toprevent evaporation of the active compounds and crystallization orprecipitation. They preferably replace 0.01 to 30% of the binder (basedon 100% of the binder employed).

The plasticizers originate from the chemical classes of phthalic acidesters, such as dibutyl, dioctyl or benzyl butyl phthalate, phosphoricacid esters, such as tributyl phosphate, adipic acid esters, such asdi-(2-ethylhexyl) adipate, stearates, such as butyl stearate or amylstearate, oleates, such as butyl oleate, glycerol ethers or highermolecular weight glycol ethers, glycerol esters and p-toluenesulphonicacid esters.

Fixing agents are based chemically on polyvinyl alkyl ethers, such as,for example, polyvinyl methyl ether or ketones, such as benzophenone orethylenebenzophenone.

Possible solvents or diluents are, in particular, also water, ifappropriate as a mixture with one or more of the abovementioned organicchemical solvents or diluents, emulsifiers and dispersing agents.

Particularly effective preservation of wood is achieved by impregnationprocesses on a large industrial scale, for example vacuum, double vacuumor pressure processes.

The ready-to-use compositions can also comprise other insecticides, ifappropriate, and also one or more fungicides, if appropriate.

Suitable additional mixing components are, preferably, the insecticidesand fungicides mentioned in WO 94/29 268. The compounds mentioned inthis document are an explicit constituent of the present application.

Especially preferred mixing components which may be mentioned areinsecticides, such as chlorpyriphos, phoxim, silafluofin, alphamethrin,cyfluthrin, cypermethrin, deltamethrin, permethrin, imidacloprid, NI-25,flufenoxuron, hexaflumuron, transfluthrin, thiacloprid, methoxyphenoxideand triflumuron,

and also fungicides, such as epoxyconazole, hexaconazole, azaconazole,propiconazole, tebuconazole, cyproconazole, metconazole, imazalil,dichlorfluanid, tolylfluanid, 3-iodo-2-propinyl-butyl carbamate,N-octyl-isothiazolin-3-one and 4,5-di-chloro-N-octylisothiazolin-3-one.

The active compound combinations according to the invention can also beused for protecting against colonization of articles, especially ships'hulls, screens, nets, constructions, quays and signalling equipment,which come into contact with seawater or brackish water.

Colonization by sessile Oligochaetae, such as Serpulidae, and byshellfish and species of the group Ledamorpha (goose barnacles), such asvarious Lepas and Scalpellum species, or by species of the groupBalanomorpha (acorn barnacles), such as Balanus or Pollicipes species,increases the frictional resistance of ships and leads as a result,through increased energy consumption and frequent spells in dry dock, toa marked increase in the operating costs.

In addition to colonization by algae, for example Ectocarpus sp. andCeramium sp., particular importance is attached to infestation bysessile Entomostraca groups, which are comprised under the nameCirripedia (cirriped crustacea).

Surprisingly, it has now been found that the active compoundcombinations according to the invention, when used alone or incombination with other active compounds, have a good antifouling(anti-colonization) effect.

By using compounds according to the invention, either alone orcombination with other active compounds, it is possible to dispense withthe use of heavy metals, such as, for example, in bis(trialkyltin)sulphides, tri-n-butyltin laurate, tri-n-butyltin chloride, copper(I)oxide, triethyltin chloride, tri-n-butyl(2-phenyl-4-chlorophenoxy)-tin,tributyltin oxide, molybdenum disulphide, antimony oxide, polymericbutyl titanate, phenyl-(bispyridine)-bismuth chloride, tri-n-butyltinfluoride, manganese ethylenebisthiocarbamate, zincdimethyldithiocarbamate, zinc ethylenebisthiocarbamate, the zinc andcopper salts of 2-pyridinethiol 1-oxide, bisdimethyldithiocarbamoylzincethylenebisthiocarbamate, zinc oxide, copper(I)ethylene-bisdithiocarbamate, copper thiocyanate, copper naphthenate andtributyltin halides, or substantially to reduce the concentration ofthese compounds.

If appropriate, the ready-to-use antifouling paints may comprise yetfurther active compounds, preferably algicides, fungicides, herbicides,molluscicides or other antifouling active compounds.

Preferred co-components for the antifouling compositions according tothe invention are:

algicides, such as

2-tert-butylamino-4-cyclopropylamino-6-methylthio-1,3,5-triazine,dichlorophen, diuron, endothal, fentin acetate, isoproturon,methabenzthiazuron, oxyfluorfen, quinoclamine and terbutryn;

fungicides, such as

cyclohexylbenzo[b]thiophenecarboxamide S,S-dioxide, dichlofluanid,fluor-folpet, 3-iodo-2-propinyl butylcarbamate, tolylfluanid and azoles,such as azaconazole, cyproconazole, epoxyconazole, hexaconazole,metconazole, propiconazole and tebuconazole;

molluscicides, such as

fentin acetate, metaldehyde, methiocarb, niclosamid, thiodicarb andtrimethacarb;

or customary active antifouling compounds, such as

4,5-dichloro-2-octyl-4-isothiazolin-3-one, diiodomethyl paratrylsulphone, 2-(N,N-dimethylthiocarbamoylthio)-5-nitrothiazyl, potassium,copper, sodium and zinc salts of 2-pyridinethiole 1-oxide, pyridinetriphenylborane, tetrabutyldistannoxane,2,3,-5,6-tetrachloro-4-(methylsulphonyl)-pyridine,2,4,5,6-tetrachloroisophthalo-nitrile, tetramethylthiuram disulphide and2,4,6-trichlorophenylmaleimide.

The antifouling compositions used comprise the active compound accordingto the invention in a concentration of from 0.001 to 50% by weight, inparticular from 0.01 to 20% by weight.

The antifouling compositions according to the invention furthermorecomprise the customary components as described, for example, in Ungerer,Chem. Ind. 1985, 37, 730-732 and Williams, Antifouling Marine Coatings,Noyes, Park Ridge, 1973.

In addition to the algicidal, fungicidal, molluscicidal and insecticidalactive compounds according to the invention, antifouling coatingcompositions comprise, in particular, binders.

Examples of acknowledged binders are polyvinyl chloride in a solventsystem, chlorinated rubber in a solvent system, acrylic resins in asolvent system especially in an aqueous system, vinyl chloride/vinylacetate copolymer systems in the form of aqueous dispersions or in theform of organic solvent systems, buta-diene/styrene/acrylonitrilerubbers, drying oils, such as linseed oil, resin esters or modified hardresins in combination with tar or bitumen, asphalt and also epoxycompounds, small amounts of chlorinated rubber, chlorinatedpolypropylene and vinyl resins.

Coating compositions also optionally include inorganic pigments, organicpigments or dyestuffs, which are preferably insoluble in salt water.Coating compositions may also comprise materials such as rosin, for acontrolled release of the active compounds. The coats may also includeplasticizers, modifying agents which influence the rheologicalproperties, and other conventional constituents. The compounds accordingto the invention or the abovementioned mixtures can also be incorporatedinto self-polishing antifouling systems.

The active compounds are also suitable for controlling animal pests, inparticular insects, arachnids and mites, which are encountered in closedrooms, such as, for example, flats, factory halls, offices, vehiclecabins and the like. They can be used alone or in combination with otheractive compounds and auxiliaries in household insecticidal products forcontrolling these pests. They are active against sensitive and resistantspecies and against all stages of development. These pests include:

From the order of the Scorpionidea, for example, Buthus occitanus.

From the order of the Acarina, for example, Argas persicus, Argasreflexus, Bryobia ssp., Dermanyssus gallinae, Glyciphagus domesticus,Ornithodorus moubat, Rhipicephalus sanguineus, Trombicula alfreddugesi,Neutrombicula autumnalis, Dermatophagoides pteronissimus,Dermatophagoides forinae.

From the order of the Araneae, for example, Aviculariidae, Araneidae.

From the order of the Opiliones, for example, Pseudoscorpiones chelifer,Pseudoscorpiones cheiridium, Opiliones phalangium.

From the order of the Isopoda, for example, Oniscus asellus, Porcellioscaber.

From the order of the Diplopoda, for example, Blaniulus guttulatus,Polydesmus spp.

From the order of the Chilopoda, for example, Geophilus spp.

From the order of the Zygentoma, for example, Ctenolepisma spp., Lepismasaccharina, Lepismodes inquilinus.

From the order of the Blattaria, for example, Blatta orientalies,Blattella germanica, Blattella asahinai, Leucophaea maderae, Panchloraspp., Parcoblatta spp., Periplaneta australasiae, Periplaneta americana,Periplaneta brunnea, Periplaneta fuliginosa, Supella longipalpa.

From the order of the Saltatoria, for example, Acheta domesticus.

From the order of the Dermaptera, for example, Forficula auricularia.

From the order of the Isoptera, for example, Kalotermes spp.,Reticulitermes spp.

From the order of the Psocoptera, for example, Lepinatus spp.,Liposcelis spp.

From the order of the Coleptera, for example, Anthrenus spp., Attagenusspp., Dermestes spp., Latheticus oryzae, Necrobia spp., Ptinus spp.,Rhizopertha dominica, Sitophilus granarius, Sitophilus oryzae,Sitophilus zeamais, Stegobium paniceum.

From the order of the Diptera, for example, Aedes aegypti, Aedesalbopictus, Aedes taeniorhynchus, Anopheles spp., Calliphoraerythrocephala, Chrysozona pluvialis, Culex quinquefasciatus, Culexpipiens, Culex tarsalis, Drosophila spp., Fannia canicularis, Muscadomestica, Phlebotomus spp., Sarcophaga carnaria, Simulium spp.,Stomoxys calcitrans, Tipula paludosa.

From the order of the Lepidoptera, for example, Achroia grisella,Galleria mellonella, Plodia interpunctella, Tinea cloacella, Tineapellionella, Tineola bisselliella.

From the order of the Siphonaptera, for example, Ctenocephalides canis,Ctenocephalides felis, Pulex irritans, Tunga penetrans, Xenopsyllacheopis.

From the order of the Hymenoptera, for example, Camponotus herculeanus,Lasius fuliginosus, Lasius niger, Lasius umbratus, Monomorium pharaonis,Paravespula spp., Tetramorium caespitum.

From the order of the Anoplura, for example, Pediculus humanus capitis,Pediculus humanus corporis, Phthirus pubis.

From the order of the Heteroptera, for example, Cimex hemipterus, Cimexlectularius, Rhodinus prolixus, Triatoma infestans.

In the field of the household insecticides, they are used alone or incombination with other suitable active compounds, such as phosphoricacid esters, carbamates, pyrethroids, growth regulators or activecompounds from other known classes of insecticide.

They are used in the form of aerosols, unpressurized sprays, for examplepump and atomizer sprays, nebulizers, foggers, foams, gels, vaporizerproducts with vaporizer tablets made of cellulose or plastic, liquidvaporizers, gel and membrane vaporizers, propeller-operated vaporizers,energyless or passive vaporizer systems, moth papers, moth sachets andmoth gels, as granules or dusts, in baits for scattering or baitstations.

The preparation and use of the active compounds according to theinvention is shown in the examples below:

PREPARATION EXAMPLES Example 1

3.3 g (0.03 mol) of methylthio N-cyano-ethane-imidate are added to 3.8 g(0.03 mol) of R-(−)-cyclohexylamine in 30 ml of methanol, and thereaction mixture is stirred at room temperature for 5 hours. Thereaction mixture is then concentrated.

This gives 5 g (86% of theory) ofR-(−)-N-cyano-N′-cyclohexyl-eth-1-yl-ethane-imid-amide having a log P(pH 2.3) of 2.19.

[The log P values were determined in accordance with EEC directive79/831 Annex V.A8 by HPLC (gradient method, acetonitrile/0.1% aqueousphosphoric acid)]

The compounds according to the invention of Table 1 are obtainedanalogously and/or in accordance with the general description of theprocess:

TABLE 1 (I)

Ex. log P (pH 2.3) No. R¹ R² R³ R⁴ or m.p. (° C.) 2

—CH₃ —OCH₃ —CN 2.73 (R isomer) 3

—CH₃ —SCH₃ —CN 2.63 (R isomer) 4

—CH₃ —NH₂ NO₂ 141 (R isomer) 5

—CH₃ —CH₃ —CN 2.20 (S isomer) 6

—CH₃ —SCH₃ —CN 2.74 (S isomer) 7

—CH₃ —OCH₃ —CN 2.73 (S isomer) 8

—CH₃ —NH₂ —NO₂ 139 (S isomer) 9

—C₂H₅ —CH₃ —CN 2.50 (R isomer) 10

—C₂H₅ —SCH₃ —CN 2.94 (R isomer) 11

—C₂H₅ —NH₂ —NO₂ 115 (R isomer) 12

—C₂H₅ —CH₃ —CN 2.51 (S isomer) 13

—C₂H₅ —SCH₃ —CN 2.94 (S isomer) 14

—C₂H₅ —NH₂ —NO₂ 107 (S isomer)

Use Examples Example A

Post-emergence Test

Solvent: 5 parts by weight of acetone Emulsifier: 1 part by weight ofalkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent, thestated amount of the emulsifier is added and the concentrate is dilutedwith water to the desired concentration.

Test plants of a height of 5-15 cm are sprayed with the preparation ofactive compound such that the particular amounts of active compounddesired are applied per unit area. The concentration of the spray liquoris chosen so that the particular amounts of active compound desired areapplied in 1000 l of water/ha.

After three weeks, the degree of damage to the plants is rated in %damage in comparison to the development of the untreated controls.

In this test, for example, the compound of Preparation Example 7effects, at an application rate of 2000 g of a.i./ha, a 90% destructionof Abutilon and a 95% destruction of Amaranthus and Sinapis, and istolerated well by maize.

Example B

Meloidogyne Test

Solvent: 4 parts by weight of acetone Emulsifier: 1 part by weight ofalkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

Containers are filled with sand, solution of active compound,Meloidogyne incognita egg/larvae suspension and lettuce seeds. Thelettuce seeds germinate and the plants develop. Galls form on the roots.

After 2 weeks, the nematicidal activity is determined by the gallformation in %. 100% means that no galls have been found; 0% activitymeans that the number of galls on the treated plants corresponds to thatof the untreated control.

In this test, for example, the compounds of Preparation Examples 1, 5and 13 effect a kill of 100%, that of Preparation Example 12 a kill of99%, that of Preparation Example 10 a kill of 98% and that ofPreparation Example 2 a kill of 95%, in each case at an exemplary activecompound concentration of 20 ppm.

Example C

Trichinella spiralis Larvae Test

Trichinella spiralis larvae are isolated from muscles of SPF/CFW1 miceand rinsed repeatedly with a Ringer solution containing Canesten (150μg/l) and sisomycin (22.6 μg/ml). Per test, about 20 larvae areincubated in 2 ml of solution of the following composition: 20 g/lcasitone, 10 g/l yeast extract, 5 g/l glucose, 0.8 g/l potassiumdihydrogenphosphate and 0.8 g/l dipotassium hydrogenphosphate pH 7.2.This solution was autoclaved, and sisomycin (15.7 mg/l) and Canesten(100 μg/l) were then added.

The compounds are dissolved in DMSO (concentration 20 mg/ml). Thesubstances are diluted with DMSO. 5 or 10 μl of DMSO solution are thenadmixed with 2 ml of incubation medium containing the 20 larvae. Themixture is incubated at 37° C. for 3 days. The anthelminthic activity isthen determined and evaluated using a scale from 0 to 3: 0=motilitycorresponds to that of the control, 1=slight motility, 2=good activity,i.e. motility highly effected to rigid, 3=full activity (all larvaedead).

In this test, for example, the compounds of Preparation Examples 2 and 7show good activity (=2) and the compound of Preparation Example 13 showsfull activity (=3), in each case at an exemplary active compoundconcentration of 100 ppm.

Example D

Nippostrongylus brasiliensis (adults) Test

Adult Nippostrongylus brasiliensis worms are isolated from the smallintestine of female Wistar rats and repeatedly rinsed with a Ringersolution containing 150 μg/l of Canesten and 23.6 μg/ml of sisomycin. Asabove under Trichinella spiralis, the preparations are taken up in DMSOand prepared. 5 μl of natural compound extract are admixed with 1 ml ofincubation medium (see above), and a total of 5 worms (either 3 male and2 female worms or vice versa) are added. The mixture is then incubatedat 37° C. for 4-5 days and the acetylcholinesterase activity in themedium is determined. Evaluation is carried out using a scale from 0 to3:0 =no activity, 1=weak activity (50-70% reduction of theacetylcholinesterase activity in the medium), 2=good activity (70-90%reduction), 3=full activity (>90% reduction).

In this test, for example, the compounds of Preparation Examples 2 and 7exhibit good activity (=2) and the compound of Preparation Example 13exhibits weak activity (=1), in each case at an exemplary activecompound concentration of 100 ppm.

What is claimed is:
 1. A compound of the formula (I)

wherein R¹ represents optionally substituted cycloalkyl, R² representsoptionally substituted alkyl or optionally substituted cycloalkyl, R³represents alkyl, alkoxy, alkylthio, amino, alkylamino or dialkylaminoand R⁴ represents cyano or nitro.
 2. A process for preparing thecompound of the formula (I) according to claim 1, comprising the stepof: reacting a compound of the formula (II)

 wherein R¹ and R² are as defined above with a compound of the formula(III)

 wherein R³ and R⁴ are as defined in claim 1, R⁵ represents alkyl and Xrepresents oxygen or sulphur in the presence of a diluent.
 3. A compoundof the formula (I) according to claim 1, wherein R¹ representsC₃-C₈-cycloalkyl which is optionally mono- to trisubstituted byidentical or different substituents selected from the group consistingof halogen, C₁-C₄-alkyl, C₁-C₄-alkoxy and C₁-C₄-alkylthio, R² representsC₁-C₄-alkyl which is optionally substituted by halogen, cyano orC₁-C₄-alkoxy or represents C₃-C₆-cycloalkyl which is optionally mono- totrisubstituted by identical or different substituents selected from thegroup consisting of halogen, C₁-C₄-alkyl, C₁-C₄-alkoxy andC₁-C₄-alkylthio, and R³ represents C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-alkylthio, amino, C₁-C₄-alkylamino or di-(C₁-C₄)-alkylamino.
 4. Acompound of the formula (I) according to claim 1, wherein R¹ representscyclopentyl or cyclohexyl, each of which is optionally mono- totrisubstituted by identical or different substituents selected from thegroup consisting of fluorine, chlorine, bromine, methyl, ethyl, methoxy,ethoxy, methylthia and ethylthio, R² represents methyl, ethyl or n- ori-propyl, each of which is optionally substituted by cyano, fluorine,chlorine, methoxy or ethoxy, or represents cyclopentyl or cyclohexyl,each of which is optionally mono- to trisubstituted by identical ordifferent substituents selected from the group consisting of fluorine,chlorine, bromine, methyl, ethyl, methoxy, ethoxy, methylthio andethylthio, and R³ represents methyl, ethyl, n- or i-propyl, n-, i-, s-or t-butyl, methoxy, ethoxy, n- or i-propoxy; methylthio, ethylthio, n-or i-propylthio, amino, methylamino, ethylamino, n- or -propylamino,ethyl-methyl-amino, dimethylamino, diethylamino, methyl-n-propyl-amino,methyl-i-propylamino, ethyl-n-propyl-amino, ethyl-i-propyl-amino,i-propyl-n-propyl-amino or diisopropylamino.
 5. A compound of theformula (I) according to claim 1, wherein R¹ represents cyclopentyl orcyclohexyl, each of which is optionally mono- or disubstituted byidentical or different substituents selected from the group consistingof chlorine, methyl and methoxy, R² represents methyl, ethyl orisopropyl and R³ represents methyl, ethyl, isopropyl, methoxy, ethoxy,isopropoxy, methylthio, ethylthio, isopropylthio, amino, methylamino,ethylamino, dimethylamino, ethylmethylamino or diethylamino.
 6. Apesticide comprising at least one compound of the formula (I) accordingto claim
 1. 7. A method for controlling animal pests and undesirablevegetation, comprising the step of allowing an effective amount of acompound of the formula (I) according to claim 1 to act on said pests,said undesirable plants and/or the habitat of said pests and/or saidundesirable plants.
 8. A herbicide comprising at least one compound ofthe formula (I) according to claim
 1. 9. A process for preparing amember selected from the group consisting of a pesticide and anherbicide, comprising the step of mixing one or more compounds of theformula (I) according to claim 1 with one or more extenders and/orsurfactants.